Target in Sight
by SuperAllTheWay
Summary: Quick one shot assassin AU where Dean is the assassin and Castiel is who he was told to follow


"Target back in line of sight." Dean Winchester spoke into his headphone mic as he began to ride his bike down the crowded street. He was disguised as a bike messenger for his assignment today. He had been told to watch a high priority business man by his boss, Crowley. Dean had been given a picture and a last name, Novak. From what Dean had seen showed no reason for him to need Dean as a tail. The guy was an attractive 30 something man who wore a trench coat that looked two sizes to big. There was nothing special about him except his insane sex hair.

Dean was used to a constant lack of information, but what he was not used to was being on babysitting duty. He was a killer, or as he preferred a trained eliminator, and he had never had to follow a mark for more than two hours before getting the green light. It had already been five hours and for the most part he just waited outside Novak's office.

Now because he was moving it was not so bad, but Dean was having trouble not getting distracted by this area of town. Novak worked in a nice office in the middle of downtown, but he had walked to an area Dean loved. The street was always full of people and the sidewalks were packed with stands selling food that ranged from fresh fruits to handmade pasta.

Dean was stuck behind an older woman when suddenly Novak turned down a narrow ally. "Shit," Dean quickly steered around the woman. He was trying to look inconspicuous as he rounded the corner. He got halfway down the ally and there was no sign of Novak so he hoped off his bike and turned it around. There stood Novak, whose face didn't seem surprised or worried at all. As for Dean he was shocked and his jaw almost hit the floor.

Castiel Novak was not an idiot. He had spotted the man on the messenger bike the second he walked out of his office building. The only reason he hadn't tried to lose the tail was because he wanted to go down to the market street and look around.

He was an tax accountant, which would normally be a very boring job but he worked for some dangerous people. The Shurley family was the wealthiest in the city and owned almost every building north of the train tracks. The family liked to think of themselves as the saving grace of this city, but they had picked up a lot of enemies on their way to the top.

Castiel had not been followed in a long while so he thought he would have some fun with it. When he stepped from the shadow of the alley behind the man, who he saw was not what he was expecting. The man was incredibly handsome unlike most hit man who for a weird reason always seem to be bald. He did his best to not show any emotion when he spoke to the man. "Why are you following me?" He took a step towards the man who instinctively backed away.

"I-Look man I'm just going to deliver-"

"Try again." Castiel gave the smallest smirks because the man didn't seem to understand that lying wouldn't help him.

"What?"

"Try answering me again, this time without lying." He took another step forward but this time the man held his ground. When the man didn't answer Castiel lets the knife he keeps in his sleeve fall into his hand. He sees the mans eyes glance down at the shinning bland, but doesn't look worried. 'He's a professionally, great' Cas thought to himself.

"I'm just a humble bike messenger." The man remarked with a knowing smirk. Cas was strangely flustered by the mans side smirk and forgot what he had said, so he decided to try a different route.

"Okay Mr. Messenger, I'm Castiel Novak." He slid the knife back in his sleeve and stuck his hand out to the other man.

"The name's Dean." This time he gave a toothy grin.

"You wouldn't happen to have a last name would you?" Castiel was flirting information out of a man who might try and kill him, and yet he did not feel any shame.

"Winchester, Dean Winchester."

The hand shake had not been expected. Dean thought the man would just threaten him a bit a then walkaway when he figured out Dean was not going to crack. This unexpected friendliness caused Dean to do something really dumb, give Castiel his real last name.

"Now I understand," He returned the smirk Dean had thrown him earlier. "You are one of Crowley's men."

"You're a lot smarter than most my jobs." Cue heartbreaking smile.

"So I'm just another job to you." Castiel took a step closer and cocked his head to the side. He was starring straight into Dean with his big blue eyes.

"Depends."

"On what."

"If I get the call to end you."

Castiel turns away but not before giving the smallest smile. "Dean, I find it amusing that you think you could get the better of me."

Dean doesn't offer him a response so Castiel gets a few yards away before turning around. "Crowley doesn't want me dead, he wants me to give him insider information on the Shurley's. I'm not surprised he chose not to inform you of this."

Right then Dean's phone began to ring, of course it was Crowley. "What do you want me to tell him?" Dean took a step forward, waiting to answer the phone.

"Offer him this, I will help him if I get to see you again Dean." Dean smiles and answers his phone. When he looks back to where Castiel had been standing, all he sees is a flash of trench coat disappear around the ally corner.


End file.
